6-Substituted penicillanic acid and derivatives thereof

Abstract

Disclosed herein are penicillanic acids and derivatives thereof which are substituted in the 6-position, processes for preparing such compounds and the utility thereof. The compounds of the invention have been found to be useful as antibacterial agents.

What is claimed is: 
     
       1. A compound of the formula: ##STR7## wherein R 3  is selected from the group consisting of lower alkyl, allyl, and benzyl; R 4  is selected from the group consisting of hydrogen, lower alkyl, benzyl, diphenylmethyl, trichloroethyl, and trimethylsilyl; and R is selected from the group consisting of ##STR8## wherein R 2  is selected from the group consisting of thienyl, phenyl, and mono and disubstituted phenyl and thienyl wherein said substituents are selected from the group consisting of chloro, bromo, nitro, lower alkyl, and lower alkoxy; and pharmaceutically acceptable salts thereof. 
     
     
       2. The compound of claim 1 wherein R 3  is lower alkyl. 
     
     
       3. The compound of claim 2 wherein R 3  is methyl and R 4  is hydrogen. 
     
     
       4. The compound of claim 3 wherein R is selected from the group consisting of ##STR9## wherein R 2  is selected from the group consisting of phenyl and thienyl. 
     
     
       5. The compound of claim 4 having the name 6-phenylacetamido-6-methylpenicillanic acid. 
     
     
       6. The compound of claim 4 having the name 6-benzamido-6-methylpenicillanic acid. 
     
     
       7. The compound of claim 1 wherein R 3  is allyl. 
     
     
       8. The compound of claim 1 wherein R 3  is benzyl and R 4  is hydrogen. 
     
     
       9. The compound of claim 8 having the name 6-phenylacetamido-6-benzylpenicillanic acid. 
     
     
       10. A compound in accordance with claim 8 having the name 6-(phenoxyacetamido)-6-benzylpenicillanic acid. 
     
     
       11. A compound in accordance with claim 4 having the name 6-(α-aminophenylacetamido)-6-methylpenicillanic acid. 
     
     
       12. A compound in accordance with claim 4 having the name 6-(phenoxyacetamido)-6-methylpenicillanic acid. 
     
     
       13. A compound in accordance with claim 4 having the name 6-[thienylacetamido]-6-methylpenicillanic acid. 
     
     
       14. A compound in accordance with claim 4 having the name 6-[2-amino-thienylacetamido]-6-methylpenicillanic acid.